5 Connecticut Small Towns to Explore with Kids

Search for pirate's treasure in the Thimble Islands.

This shoreline community is one of our favorite Connecticut staycation destinations. We call it the “Bike, Brews, and Views” day trip.  You can’t get much more “Connecticut” than family friendly breweries, stunning coastal landscape, pirates, and lobster rolls. Start the day with a leisurely cruise around the archipelago known as the Thimble Islands. Then take a bike ride along the Shoreline Greenway Trail and take in some stunning scenery. We then end our day at the Stony Creek Brewery – but make sure you stop at the Lobster Shack first to grab a lobster roll to-go (Connecticut style, of course!) 

Cut some farm-fresh flowers at Scotts Farm & Greenhouses.

It would be impossible to create this list without mentioning Essex, after all it was rated the “Best Small Town in America.” Expect winding roads, historic homes, vintage steam trains, a fantastic museum, and antiques shops. Yes, Essex is all that and it has a family friendly tap room with regular sing-a-longs.  The Griswold Inn & Tap Room is one of the oldest continuously operating inns in the country, and its nightly schedule of live music should not be missed!  In the summer, we also like to pick flowers from Scott's Farm & Greenhouses. Visitors are given clippers and a basket to fill with fresh fragrant blooms. Make sure you bring a bucket of water so these beauties will survive the trip home.

Get up close and personal with beluga whales at Mystic Aquarium. 

Come for the Aquarium & Seaport, stay for the charm. Mystic is perhaps one of the most visited locations in the state, but that doesn’t mean it lacks small town charm. In the summer, visitors swarm the streets for pizza and beluga whales, but this town is a true gem.  If your kids don’t get the whole pizza Mystic Pizza thing, just take them to Mystic Drawbridge Ice Cream, watch the kayakers and boats float by, and reminisce about simpler times. 

Enjoy a walk down the Simsbury Art Trail. 

Located about 15 miles west of Hartford, charming would aptly describe Simsbury. You can enjoy a walk around town on the Simsbury Art Trail, bike through Stratton Brook State Park, or enjoy a haunted burger at Abigail’s Grill. Don't miss the friendly farm folk at Flamig Farm too. You can’t get much more small town than that!